Visiting Portland during Winter – What To Do in Portland’s Rainy Season

Visiting Portland during Winter – What To Do in Portland’s Rainy Season

Visiting Portland During Winter

visiting portland in winter

Welcome to Portland! When I looked up a weekend in Portland, most lists were full of things to do in the Summer. But what about the people who are visiting Portland during Winter? Just because it’s not Portland’s best season, doesn’t mean there aren’t fun things to do! As a transplant (a title I take on happily from locals) I will do my best to give you a wonderful guide for your stay in Portland. If you’re like me, you want to be introduced to the spots locals enjoy but also see some of the iconic destinations. For this post, I am going to try to shoot for a mixture of tourist hotspots and places that might be overlooked. All opinions are my own.

Coffee!

First thing is first, coffee. Always coffee. Especially while visiting Portland during Winter. Portland is one of the country’s leading places in coffee, so I am sure you expect to be wowed by your cup of joe while you are in town!

Tourist Hot Spot:

If you’re visiting Portland, I bet you’ve heard of Stumptown. They have grown a large following for providing high quality coffee in a relaxing atmosphere. There are several cafes across the Portland area, but my favorite is the one that is attached to the Ace Hotel in downtown, Portland

visiting portland during winter

visiting portland during winter

visiting portland during winter
Ace Hotel, Downtown Portland

Both the cafe and the Ace Hotel lounge are quite lovely. It’s the perfect place to sit and have a cup of coffee. Buy a bag of beans and Stumptown will give you a complimentary cup that you can enjoy in their cafe or in the hotel lounge. Engage in some people watching or pick up one of the many local newspapers sprawled out on their large coffee table.

Like a Local:

I was just introduced to this coffeeshop recently and I loved it so much I had to edit this post and add it to the list. Groundwork Coffee started in California and recently opened up an insanely gorgeous coffee shop in Portland. Groundwork Coffee serves organic, fair trade coffee and is dedicated to community involvement. I was invited to a brunch with a few other Instagrammers/bloggers and the moment I walked in the door I was in love.

visiting portland during winter

visiting portland during winter

This intimate space has gorgeous garage doors that allows for some wonderful lighting. I had the most incredible iced mocha of my life and some delicious gourmet avocado toast for breakfast. This is a fairly undiscovered spot on one of Portland’s most beloved streets. I will definitely be visiting this coffeeshop very often.

visiting portland during winter
Groundwork Coffee, SE Hawthorne

Kainos Coffee 

Kainos Coffee is a local coffee shop owned by two best friends who also love to give back to the community. The owners donate 21% of their earnings to charity to help kids in need. This bright and intimate coffee shop offers a variety of caffeinated beverages (I recommend the bourbon maple latte) accompanied with lovely latte art.

visiting portland during winter

This place really has it all. Delicious drinks, a great atmosphere, generous owners, and a kick-ass wall.

visiting portland during winter

In Case You Don’t Like Coffee:

Tea Bar

visiting portland during winter
Tea Bar, NE Killingsworth St

If you’re visiting Portland during Winter, there really is no end to your need for warm beverages. If you’re more of a tea drinker, look no further than Tea Bar. This place is AMAZING. As a huge coffee addict, sometimes it’s almost hard not to ditch cafe hopping around the city and just post up at a Tea Bar. They offer the best boba tea in the city with flavors like matcha, cinnamon, vanilla rose, and my favorite, lavender. All these flavors come both hot and cold! They also carry loose leaf teas, lattes, chais, and hot toddys. Their staff is knowledgeable and charismatic and their stores all share a bright and simplistic design that stuns. No wonder they were recently featured in Vogue as some of the best boba tea in the country!

visiting portland during winter
Tea Bar, Pearl District

Doughnuts

Before I moved to Portland I probably had a doughnut once a year. Now I have them more like once a month. If you absolutely love doughnuts, then why not spend your time here trying all the doughnut shops Portland has to offer? If you just want to eat the best of the best, then here are the doughnut shops you can’t miss.

Tourist Hot Spot:

visiting portland during winter
Blue Star Donuts, Portland (source)

Blue Star Donuts‘s motto is “quality over quantity” and they never stray from that belief. Their shops are filled with decadent doughnuts that will make you feel like royalty. (If royalty ate doughtnuts.) Some of their flavors include blueberry bourbon basil, lemon poppy-seed, maple bacon, and my favorite valrhona chocolate crunch (all shown above.)

Prepare yourself, these doughnuts aren’t cheap (around $3). But they are made with quality ingredients and made fresh every day. Parking can be hard to find and there will most likely be a line. I recommend visiting the newly opened Blue Star in the SW waterfront area. There is ample parking and I have yet to see any line at this location. (Check their website for the address if you can’t find it in google maps.)

Like a Local:

My favorite doughnut shop in Portland is by far Pip’s Original. This fantastic shop is run by a couple who deeply believe in community and taking care of each other. Pip’s provides you with warm, made to order doughnuts that will melt in your mouth. They have less variety than the other shops, but they don’t need a wide range of flavors when the ones they have taste so good.

visiting portland during winter
Pip’s Original Doughtnuts, Portland

Mix and match with flavors like Nutella, cinnamon sugar, and honey. Need a little extra warmth? (You are visiting Portland during Winter, after all!) Order a flight of their incredible chai. At Pip’s, it’ll almost feel like you are visiting an (oddly populated) cabin in the woods. The decor is rustic and cute with knick knacks and string lights hanging from the walls. Best spot in the house is by a window. Like Blue Star, be prepared to wait in line, it’s a thing you will find happens a lot in Portland. If it feels a little cramped inside, simply ask for a to-go order. You’ll receive a box with a cute message inscribed! If it happens to be your birthday (or 7 business days after) Pip’s will give you a dozen doughnuts on the house. Now if that isn’t the type of place you wanna love, I don’t know what is.

visiting portland during winter
Pip’s Original Doughnuts, Portland

In Case You Don’t Like Doughnuts

visiting portland during winter
Moonstruck Chocolates

Moonstruck Chocolate offers some of the most decadent chocolate, cookies, and beverages I have ever had. I’ve tried nearly everything on their menu (I worked here for a brief amount of time) and honest to god, anything you get here will blow your senses away. Their truffles and chocolates not only taste amazing, they are beautiful to look at. If you have kids traveling with you, they will be so excited to see the cute chocolate animals they can choose from. If you’re looking for a drink to satisfy your sweet tooth, you’re in luck, they have it all. Try their Mayan hot chocolate for an out of this world taste.

Recently, Moonstruck’s NW location was unfortunately destroyed in a gas leak explosion. While they are repairing, the only location they have open in Portland is the one that can be found on SW Alder. This cafe is their smallest location, so if you have a group of more than 2, don’t expect to find a seating area.

Sight Seeing

Since you are visiting Portland during Winter, it will most likely be rainy and cool outside. As long as you have a rain jacket and sensible shoes, you should be able to face the great outdoors. But even on the nicest days, it still feels good to get indoors for a bit. Here’s a mixture of outdoor and indoor activities you can enjoy!

Tourist Hot Spots

visiting portland during winter
Multnomah Falls, Oregon

If you have access to a car, take the 40 minute drive (traffic permitting) to Multnomah Falls. This iconic 620 ft waterfall is typically a must see on any Portland trip. Depending on weather, you can take a short hike to the bridge that overlooks the lower half of the falls, or continue further to the final viewing area at the top. Sometimes places that you have been dreaming to see for a while don’t live up to the hype, but Multnomah Falls is jaw dropping and more than lived up to the photos I had seen before visiting.

We’ve visited many times since we moved here. Twice the hike was very muddy and had a build up of snow. If you plan on hiking up (even to the short bridge) make sure you wear sensible shoes. I saw a lot of people fall while they were walking on the trail because they were in Uggs or Converses. If there does happen to be snow, I wouldn’t recommend going on the trail unless you have experience walking on narrow paths covered in snow and ice. You still get a gorgeous photo opportunity at the lower viewing area.

visiting portland during winter
Andy Warhol Exhibit, Portland Art Museum

The Portland Art Museum is a great choice for a gray, rainy day in Portland. The museum circulates exhibitions every few months, keeping it fresh and interesting. The price of admission is a little steep at $20 a ticket. If you are looking to enter on a budget, Friday night tickets are only $5 each! Attached to the museum is a cafe called Musuem Grounds which offers Stumptown coffee and local pastries and bagels.

Like A Local

visiting portland during winter
Soaking Pool, McMenamins Kennedy School

Start your day off right and head to McMenamins Kennedy School and indulge in their salt water based soaking pool. This heated pool is the perfect remedy for anyone’s winter blues. Sit and relax with a mimosa or a bloody mary and let your stress melt away – for only $5 an hour! Make sure to bring your own towels and a photo ID for access to the pool. If you are traveling with children, be aware that children are not permitted in the pool until 11 AM. If you are child free, either visit the pool at 10 AM or 12 PM for a quieter experience.

Grab A Drink

Tourist Hot Spot:

visiting portland during winter

10 Barrel was one of the first places I had a drink when I moved to Portland and it’s still one of my favorite spots to bring visiting friends and family to. 10 Barrel, another company that loves to give back to the community (are you seeing a pattern here) has some of the best beers on tap and some of the tastiest pub food on their menu. Grab a seat at the bar and chat up one of the friendly bartenders who will make you feel at home and help you navigate your way through their vast selection of drinks. If it’s a particularly nice day, head upstairs to their beautiful outdoor deck!

visiting portland during winter
10 Barrel Brewing, Pearl District

Like a Local:

visiting portland during winter
Portland City Grill, Portland

Wrap up your day with happy hour at Portland City Grill. An absolutely magnificent view of the city will have your group snapping endless photos in between cocktails. At 30 stories high, Portland City Grill’s lounge offers open seating at the bar and the small booths next to the window. Happy hour runs from 5-7 offering cheap cocktails, wine, and beer. Sip on drinks and share some small plates while you gaze out at the glittering lights of PDX.

Visiting in the Month of December:

If you’re in town visiting for the holidays, don’t miss these events while you’re in town!

Santa Slices at Sizzle Pie:

visiting portland during winter
Sizzle Pie, Portland

If you tell me you’ve never wanted to finish an entire pizza by yourself, you’re lying. Well, here’s your chance! Sizzle Pie fits an entire 18″ pizza into a single slice for their holiday special – Santa Slices. You can get these amazing slices of pizza from December 17th-24th. Make sure to check which of their locations is currently offering it before you go.

Zoo Lights at The Oregon Zoo:

visiting portland during winter
Zoo Lights, The Oregon Zoo

Do you love Christmas lights? Zoo Lights at the Oregon Zoo has a seriously impressive display of lights. With over 1 million lights, Zoo Lights puts on quite a show with animated displays, 2 operating trains, and a walk through tunnel. This is a very family friendly event that both kids and adults will love. In early December, weekdays are value nights which offer $10 tickets. Otherwise tickets are $15 and do not include anything other than entry into the event.

 

Peacock Lane:

$15 sound a little too expensive? Not a problem. Starting December 15th, Peacock Lane is a street full of houses in the highest of Christmas spirits. Come walk along Peacock Lane and admire the dedication these families put forth to bring cheer to Portland locals. You will even be offered complimentary hot cocoa or hot cider while you stroll along the street picking out your favorite decorated house. This is a Portland tradition that locals hold dear to their hearts. Make sure to be respectful of the area considering that these are people’s homes. Think before you go into someone’s yard to snap a photo.

 

I hope you enjoy your stay in Portland! No matter the season, this is an incredible city with a lot to offer. Have you visited before and have any other tips to add to my post? Was this post helpful for you during your stay. Always hoping to hear your thoughts!

-Ryan